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Propargyl alcohol → [3-(3-Hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl ester

HRID 1352863
ノート
印刷プレビュー

反応式

HRID 1352863 の反応式
I[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH2:17]([OH:20])[C:18]#[CH:19].C(OCC)(=O)C>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:20][CH2:17][C:18]#[C:19][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 7859Propargyl alcoholHCID 8857Ethyl AcetateHCID 52449400t-Butyl (3-iodophenoxy)acetate

生成物 1

HCID 54255612[3-(3-Hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl ester収率 68.2%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 178418476
HCID 178418476、化合物
触媒
HCID 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

The compound (1.00 g, 3.00 mmol) of Example 22-1 was dissolved in triethylamine (30 ml) under an atmosphere of nitrogen. Thereto were added propargyl alcohol (0.35 ml, 6.00 mmol), copper(I) iodide (6.00 mg, 30.0 μmol) and dichlorobis(triphenylphosphine)palladium (II) (42.0 mg, 60.0 μmol) and the mixture was stirred for 1 hour at 70° C. The mixture was cooled and thereto was added ethyl acetate. The mixture was washed with 10% aqueous citric acid solution, water, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order and dried over sodium sulfate. The solvent was removed and purified with silica gel chromatography (hexane:ethyl acetate, 3:1–2:1) to give the subject compound as a yellow oil(537 mg, 68%).

後処理

  1. temperatureThe mixture was cooled
  2. washThe mixture was washed with 10% aqueous citric acid solution, water
  3. dry with materialan aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order and dried over sodium sulfate
  4. customThe solvent was removed
  5. custompurified with silica gel chromatography (hexane:ethyl acetate, 3:1–2:1)

出典と根拠

ORDレコード
ord-a2059c51137b4639919fccc3fccc2abe
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07220773B2

反応ノート

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